3-Bromo-1-(trimethylsilyl)-1-propyne → Diethyl (3-trimethylsilylprop-2-ynyl)phosphonate

Participants

Reaction Steps

Into a solution of LiHMDS (1M in THF, 63.8 mL, 63.8 mmol) in anhydrous THF (162 mL) was added dropwise under stirring at −10° C. in nitrogen atmosphere diethyl phosphite (7.4 mL, 63.8 mmol). The obtained solution was stirred at the same temperature for 20 min. Afterwards, 3-bromo-1-trimethylsilyl-1-propyne (10 mL, 63.8 mmol) was dropped into and the reaction mixture was stirred at −10° C. for 2 h., then quenched with water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford 14.86 g of the title product.

Provenance & Evidence